How to scale a sales org to $50M ARR | Ian Grace (Ocrolus)

In this episode, I sit down with Ian Grace, VP of Sales at Ocrolus, to talk about what it takes to turn a sales team around, coach reps more effectively, and build a repeatable process that actually drives revenue. Ian breaks down how he came into Ocrolus during a brutal stretch for the mortgage industry and helped overhaul the sales motion by implementing forecasting, deal coaching, MEDDPICC, and a blended approach built around gap selling and challenger principles. He explains why great discovery is still the foundation of winning deals, and why too many reps stop at surface-level pain instead of digging until they understand the real business impact in dollars. We also get tactical on pipeline management, leadership, and the use of AI inside modern sales organizations. Ian shares why thin pipeline is usually a prospecting discipline problem before it is anything else, how managers can coach reps without taking deals over for them, and what changed in his own leadership when he stopped thinking about himself and started thinking more about how to truly support his team. He also talks through how Ocrolus is experimenting with Claude and Gong to score calls, evaluate reps against sales frameworks, and create more precise coaching feedback at scale. TOPICS WE COVER How Ian helped improve win rates at Ocrolus by implementing forecasting, deal coaching, MEDDPICC, and stronger day-to-day sales habits  Why shallow discovery kills deals, and how the best reps turn pain into real dollar impact that creates urgency  The most common reasons deals stall, including weak champions, lack of multithreading, and incomplete discovery  Why pipeline problems usually start with prospecting discipline, and how Ian thinks about quantity before quality  What strong sales coaching looks like in practice, including call review, live feedback, and helping reps improve without taking over for them  How Ian is using tools like Gong and Claude to score calls, evaluate reps against sales frameworks, and create more actionable coaching feedback ABOUT THE GUESTIan Grace is the VP of Sales at Ocrolus, an AI analytics and decision platform that helps lenders make faster, better decisions using financial documents. He oversees the Sales Development, Inside/Mid-Market Sales, and Sales Engineering Teams. Prior to Ocrolus he was a Senior Director at automotiveMastermind Inc. and also directed branch banking, sales, and marketing operations for a $76MM credit union in an executive role.LINKSConnect with me: https://www.linkedin.com/in/carter-armendarez/ Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/ Learn more about Ocrolus: https://www.ocrolus.com/